In the hushed corners of fading Irish bars, the old-timers still reminisce about a time when Irish names commanded respect – and fear – in the American underworld. They raise a glass of Jameson, a wistful silence falling as they recall vanished friends and a homeland left behind, a world drastically different from today.
Once, Irish gangs thrived across the nation. From the brutal clashes between Dion O’Bannion and Bugs Moran against Al Capone in Chicago, to the ruthless Winter Hill Gang in Boston, the West End Gang in Montreal, and most infamously, the Westies in New York City, Irish racketeers were a dominant force.
But the story isn’t simply one of violence. Like many immigrant groups, the Irish gradually climbed the socio-economic ladder, choosing legitimacy over a life of crime. Yet, in the 1980s, the Westies, entrenched in the gritty streets of Hell’s Kitchen, conceived a plan so daring, so reckless, it nearly reshaped the landscape of New York’s organized crime.
It began with Jimmy Coonan, a rising thug who orchestrated the hit on Mickey Spillane, a prominent Irish mobster, through the volatile Roy Demeo of the Gambino family. Coonan’s most potent weapon wasn’t a gun, but Mickey Featherstone, a Vietnam veteran haunted by demons and capable of unimaginable brutality.
The Westies were a relatively small crew, numbering between twenty and sixty members. They controlled unions at iconic venues like Madison Square Garden and the New York Coliseum, supplemented their income with bookmaking and loansharking, and readily offered their services as enforcers for other families.
Their reputation for savagery preceded them. A Gambino wiseguy, overheard on a police wiretap, succinctly captured the prevailing sentiment: “These guys are f—ing crazy.” It was a backhanded compliment, a testament to their unpredictable and terrifying nature.
Paul Castellano, the powerful head of the Gambino family, preferred order and control. He wasn’t a “street guy” and viewed the Westies’ chaotic violence as a liability. He summoned Jimmy Coonan to a meeting at a Brooklyn restaurant, hoping to bring the Irish gang under his wing.
Coonan, inherently distrustful of the Italians, brought Featherstone along as a silent, menacing deterrent. He suspected a trap, and Featherstone was there to ensure he wasn’t walking into one.
Unbeknownst to Castellano, Coonan had a far more audacious plan brewing. A large hit team, armed with machine guns and grenades, lay in wait nearby. If Coonan and Featherstone didn’t return within two hours, they were to unleash a massacre inside the restaurant, eliminating everyone present.
The meeting began tensely. The Gambinos questioned Coonan about the disappearance of Ruby Stein, a loan shark found brutally murdered, chopped into pieces. Coonan vehemently denied any involvement, a lie Castellano surprisingly accepted, offering the Westies “protection” under the Italian umbrella.
Castellano laid down the law: the Westies needed to curb their “cowboy” tactics and operate under his authority. Any future violence required his approval. Then, remarkably, they settled in for a leisurely dinner, enjoying pasta, veal, and copious amounts of wine.
As the evening progressed, Coonan glanced at his watch and realized the deadline for his hit squad had passed. He excused himself, expecting to find his men poised for carnage. Instead, he discovered them deep in a whiskey-fueled haze.
His hit team, after much deliberation and several more glasses of Irish Whiskey, had decided a more prudent course of action was patience and another drink. The impending bloodbath had been averted, not by strategy, but by intoxication.
The underworld was shifting in the late 1970s and early 1980s, and the Westies’ reign was nearing its end. The turning point came with Mickey Featherstone. Driven by fear for his own life, he broke Omertà, revealing the Westies’ bloody history and countless crimes in a New York City courtroom.
His testimony effectively dismantled the century-old criminal syndicate, ending the era of romanticized Irish gangsters and the cultural tropes associated with them. The Irish, for the most part, had truly gone legitimate.
Castellano himself wouldn’t last much longer, gunned down on a Manhattan street in 1985. The RICO laws then systematically dismantled the remaining vestiges of the old order, forcing gangsters to betray their code of silence.
The Irish found new avenues of power in the police and fire departments, civil service, and politics, gradually controlling municipal and state governments, culminating in the presidency in 1960. Prosperity, ultimately, proved a more potent force than any criminal enterprise.
Whitey Bulger, the last significant Irish crime boss, remained an outlier. He was brutally murdered in prison in 2018, a violent end to a long and notorious career. But even Bulger couldn’t withstand the tide of progress and respectability.
The age of the Irish mob is over, as definitively closed as the final scene of a classic gangster film. It’s a chapter of history, as distant and faded as James Cagney’s character in *White Heat*.
As St. Patrick’s Day arrives, a reminder echoes from the pages of another story: “Give us a drink. And give some to those Irish hoodlums down there.” A toast, perhaps, to a bygone era, but one best left in the past.
